Amphiphilic nitrogen containing imidazolinium derivative compounds and uses

Abstract

Amphiphiles containing an imidazdinium ring system are provided that are non-toxic to the host mammal. The amphiphiles are used to produce liposomes useful as carriers for delivering macromolecules intracellularly.

What is claimed is: 
     
       1. A nitrogen-containing amphiphile of the formula: ##STR6## wherein each R and R 1  independently is a straight-chain, aliphatic hydrocarbyl group of 11 to 29 carbon atoms inclusive. 
     
     
       2. The amphiphile of claim 1 wherein R independently has from 13 to 23 carbon atoms inclusive. 
     
     
       3. The amphiphile of claim 1 wherein R is heptadecyl or R 1  is octadecyl. 
     
     
       4. The amphiphile of claim 1 wherein R is tridecyl or R 1  is tetradecyl. 
     
     
       5. The amphiphile of claim 1 wherein R is pentadecyl or R 1  is hexadecyl. 
     
     
       6. The amphiphile of claim 1 wherein R is heptadecenyl or R 1  is octadecyl. 
     
     
       7. The amphiphile of claim 1 wherein said amphiphile is 1- 9-(Z)-octadecenoyloxyethyl!-2- 8-(Z)-heptadecenyl!-3-hydroxyethylimidazolinium. 
     
     
       8. A method for synthesizing an imidazolinium ion, which comprises: heating a precursor compound of formula ##STR7## in an organic solvent at a temperature above the boiling point of water, wherein each of R and R 1  independently represents an organic group such that said precursor compound is soluble in said solvent and said R and R 1  are stable against reaction in said solvent at said temperature.   
     
     
       9. The method of claim 8, wherein said solvent is a protic solvent. 
     
     
       10. The method of claim 8, wherein said heating occurs in the presence of an acid. 
     
     
       11. The method of claim 10, wherein said acid is HCl.